Chicago: The City That Reminded Me Most of Boston
Of all the cities we’ve visited, Chicago reminded me the most of Boston, which surprised me because it obviously isn’t on the ocean.
Here are a few things we especially loved.
Millennium Park: The Bean and the Fountains
Cloud Gate, better known as The Bean, is much larger than it appears in pictures. Its mirrored surface reflects the skyline and everyone standing nearby. My kids immediately start running around it, trying to see themselves from every angle.
Right nearby is Crown Fountain, the plaza with the tall glass towers that display faces of Chicago residents. Every few minutes, the two tower faces “spit” water from their mouths.
Just next to Millennium Park is Maggie Daley Park.
The Chicago Riverwalk
The path runs along the river through the heart of downtown, with bridges, boats passing by, and incredible views of the surrounding architecture.
Chicago River Architecture Boat Tour
I loved this tour, even if you’re not into architecture, it's still fascinating. The guides explain how Chicago rebuilt itself after the Great Chicago Fire of 1871, which is why the skyline features such a variety of architectural styles. This tour also reveals the truth about Chicago’s nickname, the “Windy City.”
It actually has nothing to do with the weather. The nickname originated in the late 1800s and referred to Chicago politicians who were known for being “windy” or full of hot air.
Navy Pier
We also spent a lot of time exploring Navy Pier, which is right on Lake Michigan. The pier has restaurants, shops, boat tours, and great views of the skyline and lake. It’s lively and definitely geared toward visitors, but it’s still worth walking around.
Inside the pier, we wandered through Crystal Gardens, a huge glass atrium filled with palm trees and tropical plants. It felt like walking into a greenhouse right in the middle of the city.
One of the kids’ favorite activities was the Seadog Extreme boat ride. A high-speed ride out onto Lake Michigan with music, sharp turns, and a few splashes along the way. It’s fast, loud, and definitely not a relaxing boat cruise.
While we were there, we rode the Centennial Wheel, the giant Ferris wheel at the end of the pier, visited the children’s museum, and let the kids splash around at Polk Bros Park.
Polk Bros Park
Lincoln Park Zoo
The zoo was bigger than I expected, and it’s pretty cool that it’s located right in the city, and admission is free. You can literally just walk in while exploring the neighborhood.
I always feel conflicted about zoos, and I felt that here too, but it is impressive how seamlessly it’s integrated into the city. It almost feels like the zoo is just another part of the park.
If you have a little extra time in Chicago, there are a few more things worth checking out.
The views from the 360 Chicago Observation Deck are incredible, especially if you try the TILT experience, where a glass platform slowly tilts outward over the city.
From there, it’s an easy walk to the Magnificent Mile, Chicago’s famous shopping stretch along Michigan Avenue, filled with stores, restaurants, and beautiful historic buildings.
Sports fans might also enjoy stopping by Wrigley Field, one of the oldest and most iconic baseball stadiums in the country.
And of course, before leaving Chicago, you should try deep-dish pizza. It’s completely different from the pizza we’re used to in New England, thick crust, layers of cheese and toppings, and the sauce on top, it’s a fork-and-knife situation.
For anyone living on the South Shore, Chicago makes for a great, easy-to-get-to city trip.